Top Tech Jobs & Startup Jobs in Chicago, IL

Handle parent support tickets in Zendesk, answering questions about schedules, billing, academics, athletics, and campus logistics. Resolve issues end to end, coordinate escalations, maintain accurate ticket tagging and macros, identify recurring problems, and communicate clearly and warmly. The role requires reliable full-time coverage during U.S. Central Time business hours and includes using AI tools to improve response efficiency.

Build and close outbound enterprise sales pipelines for a new payroll-giving scholarship program. Sell consultatively to HR, Total Rewards, Benefits, CSR, Finance, Legal, Payroll, and executive stakeholders at employers with 10,000+ employees. Explain payroll deduction and tax-credit mechanics, manage complex implementations, support successful program launches, and capture market intelligence to shape messaging, ideal customer profiles, and the go-to-market playbook.

Provide first-line remote technical support to students and parents for devices and learning platforms via email, chat, ticketing, and phone. Troubleshoot hardware/software/connectivity across Mac, Windows, iOS, and Chromebooks, escalate complex issues, maintain knowledge base articles, and report on ticket volume and trends. Weekend coverage and clear written communication required.

Provide advisory services to assess and improve ManageEngine Endpoint Central for a macOS fleet: recommend packaging and deployment best practices (PKG/DMG), patch/update scheduling, repository/version control, integration with MDM/ITSM/security tools, troubleshoot complex deployment issues, improve documentation, and coach internal IT staff during periodic strategy check-ins.

Own end-to-end Meta (Facebook & Instagram) paid acquisition for Sports Academy Games: plan, build, launch, optimize, and scale campaigns to drive sign-ups and active players. Develop K-12 targeting strategies, run structured creative tests, brief creative, track CAC/ROAS/sign-ups, report insights, and adapt strategy for platform and attribution changes.